The short answer: start with the people, not the place. Decide what each generation needs to enjoy the trip, choose a base that gives everyone space and a shared table, and plan fewer things than you think. A milestone trip succeeds when the grandparents are comfortable, the children are busy and the parents are actually on holiday.
Why these trips are everywhere right now
In the 2026 Virtuoso Luxe Report, "celebrating a milestone" was the number one reason affluent people travel, and family and multigenerational travel were the two biggest trends of the year. In Virtuoso’s July 2026 survey of nearly 800 advisors, multigenerational and family travel together led the trip types drawing increased client requests, cited by 69% of respondents.
A 70th birthday, a golden anniversary or a graduation has become a reason to gather everyone in one beautiful place.
Step 1: Decide what the trip is for
Is it about one evening, a celebration dinner, or about a week of time together? The answer changes everything.
If the celebration is the heart, choose a place with a setting worthy of that one night: a terrace, a garden, a private room.
If time together is the heart, choose a base where everyone can be together without being on top of each other.
Step 2: Choose the base: villa, resort or both
A private villa gives you a shared kitchen table, a pool that belongs to you and no other guests. It works well when the group is close and enjoys being together. You will need to think about staffing, cooking and driving. Our villa rentals page explains the options.
A resort gives everyone independence: kids' clubs, spa, several restaurants and someone else handling every detail. It suits groups where different generations want different days.
A resort with villas or connecting suites is often the best of both. Ask early, because these are usually the first rooms to go.
Step 3: Plan around the grandparents' comfort
A small detail that changes the whole experience: how far the rooms are from the restaurant and the pool. Stairs, slopes and long walks matter more than star ratings.
Also think about flights. A direct flight and one base is easier for older travellers than a multi-stop journey.
Step 4: Give the children a reason to love it
Children remember doing things, not views. Look for one hands-on experience a day at most: a cooking class, a boat, a beach, a farm visit. Our guide to taking children on a luxury train shows how to keep even a formal experience fun for them.
Step 5: Protect everyone's free time
The most common mistake is planning every day as a group. We suggest a rhythm: one shared highlight each day, then free time. A shared dinner most nights, with one or two nights off for couples.
Step 6: Make the milestone moment special
This is where thoughtful planning makes the difference:
A private dinner set up somewhere unexpected: a vineyard, a garden, a boat.
A photographer for one hour, so the host is in the photos too.
A small surprise for each generation.
If a couple is marking an anniversary inside a family trip, a short vow renewal can be a beautiful addition.
Where these trips work well
Provence, where a resort like Terre Blanche offers villas, golf and space for every age. See our guide for families with grandparents.
Puglia, with its farmhouse hotels, olive groves and easy beach days.
Dubrovnik, for a city, a coast and a boat in one trip. See our family review.
A river cruise, where everyone unpacks once and the scenery changes every day.
Planning your celebration
If you are planning a celebration like this, our personal group travel and family vacations pages are good places to start the conversation.
How far ahead should we plan a multigenerational trip?
For summer or a specific celebration date, we suggest starting 12 to 18 months ahead. Villas and connecting rooms go first.
Who should make the decisions?
One person, usually the host, should hold the final decisions, with everyone else giving input early.
Is a villa or a resort better for three generations?
If the group loves cooking and being together, a villa. If different ages want different days, a resort. If you are unsure, a resort with villas.
Csilla Dali
Founder & Lead Travel Advisor
Itineraries to consider
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